Enzymatic glycosylation using 6-O-acylated sugar donors and acceptors: beta-N-acetylhexosaminidase-catalysed synthesis of 6-O,N,N'-triacetylchitobiose and 6'-O,N,N'-triacetylchitobiose

L Husáková; S Riva; M Casali; S Nicotra; M Kuzma; Z Hunková; V Kren

doi:10.1016/s0008-6215(01)00027-1

Enzymatic glycosylation using 6-O-acylated sugar donors and acceptors: beta-N-acetylhexosaminidase-catalysed synthesis of 6-O,N,N'-triacetylchitobiose and 6'-O,N,N'-triacetylchitobiose

Carbohydr Res. 2001 Mar 22;331(2):143-8. doi: 10.1016/s0008-6215(01)00027-1.

Authors

L Husáková¹, S Riva, M Casali, S Nicotra, M Kuzma, Z Hunková, V Kren

Affiliation

¹ Laboratory of Biotransformation, Institute of Microbiology, Academy of Sciences of the Czech Republic, Prague.

PMID: 11322728
DOI: 10.1016/s0008-6215(01)00027-1

Abstract

p-Nitrophenyl 6-O-acetyl-2-acetamido-2-deoxy-beta-D-glucopyranoside (5a) was used as the glycosyl donor in a beta-N-acetylhexosaminidase-catalysed (from Penicillium brasilianum) glycosylation of GlcNAc yielding 6'-O,N,N'-triacetylchitobiose (6), while 6-O-acetyl-2-acetamido-2-deoxy-beta-D-glucopyranose (3a) served as a selectively protected acceptor in a transglycosylation reaction catalysed by the same enzyme to yield 6-O,N,N'-triacetylchitobiose (4).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aspergillus oryzae / enzymology
Disaccharides / chemical synthesis*
Disaccharides / chemistry
Glycosylation
Molecular Structure
Penicillium / enzymology
beta-N-Acetylhexosaminidases / chemistry
beta-N-Acetylhexosaminidases / isolation & purification
beta-N-Acetylhexosaminidases / metabolism*

Substances

Disaccharides
chitobiose
beta-N-Acetylhexosaminidases